title: Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.
abstract: A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
authors.forename: Chi Wai
authors.initials: CW
authors.lastname: Cheung
authors.forename: David S
authors.initials: DS
authors.lastname: Surry
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000641:Ammonia / Q000737:chemistry*; D002384:Catalysis; D006219:Halogens / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
chemical_list: D006219:Halogens; D008024:Ligands; D010720:Phosphines; D010165:Palladium; D000641:Ammonia